15 questions about
regrets
Pick one and start there. You don't have to go in order.
- 1
"What's your biggest regret — and have you made peace with it?"
- 2
"Is there a path you didn't take that you still think about?"
- 3
"What's something you wish you'd done sooner?"
- 4
"Is there a relationship you regret losing or ending?"
- 5
"What's something you said (or didn't say) that you can't take back?"
- 6
"What's a choice you made that turned out to be a mistake — and what did you learn?"
- 7
"What do you most want to avoid regretting when you're older?"
- 8
"Is there something in our relationship that you regret?"
- 9
"What's the regret that visits you most often?"
- 10
"What's a regret you've worked through and genuinely moved past?"
- 11
"Is there a person you owe an apology to that you haven't given?"
- 12
"Is there a version of yourself you gave up that you sometimes miss?"
- 13
"What do you regret not appreciating when you had it?"
- 14
"What would you do differently in your career if you could?"
- 15
"What's something you wish you'd been brave enough to try?"
How to use these
conversation starters
Over dinner
Pick one question at the start of the meal. Let the conversation lead where it wants.
On a long drive
No eye contact makes some questions easier. Road trips are perfect for depth.
Before sleep
One question each before the lights go out. This becomes a ritual you'll both love.
On a walk
Walking side by side reduces pressure. The movement helps the conversation flow.
Sunday morning
Slow morning, no agenda. Phones down. One question over coffee.
In the app
Log your answers in Relationship App: Love Story. Look back on them together.
Keep the conversation
going every day.
Daily prompts, mood check-ins, love notes, and a shared memory of every conversation you have together.